US6090939A - Process for preparing polyisocyanates containing iminooxadiazinedione groups - Google Patents

Process for preparing polyisocyanates containing iminooxadiazinedione groups Download PDF

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US6090939A
US6090939A US09/318,537 US31853799A US6090939A US 6090939 A US6090939 A US 6090939A US 31853799 A US31853799 A US 31853799A US 6090939 A US6090939 A US 6090939A
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mixture
trimerization catalyst
groups
molecular weight
average molecular
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Frank Richter
Eberhard Stelter
Wilfried Litz
Stefan Groth
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Covestro Deutschland AG
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Bayer AG
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Priority claimed from DE1998124490 external-priority patent/DE19824490A1/de
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
    • C08G18/022—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing isocyanurate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C07D251/34—Cyanuric or isocyanuric esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
    • C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
    • C07D273/04—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/166—Catalysts not provided for in the groups C08G18/18 - C08G18/26
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/7875—Nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
    • C08G18/7887—Nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring having two nitrogen atoms in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups

Definitions

  • the present invention relates to a process for the preparation of trimerized polyisocyanates that contain iminooxadiazinedione groups in the presence of a quaternary phosphonium polyfluoride trimerization catalyst.
  • Polyisocyanates containing iminooxadiazinedione groups are valuable, high quality raw materials, which may be used, e.g., for the manufacture of polyurethane lacquers and coatings (e.g. DE-A 19,611,849). These polyisocyanates are present as a subsidiary component in the well known polyisocyanates containing isocyanurate groups (symmetric trimers).
  • Isocyanate oligomers having a significantly increased iminooxadiazinedione content are the subject of DE-A 19,611,849. Their advantageous properties, for example, as a raw material for the manufacture of polyurethane lacquers and coatings, are described.
  • (di)isocyanate oligomers having at least three NCO groups polyisocyanates containing iminooxadiazinedione groups have the lowest viscosity.
  • trimer mixture is defined as the sum of symmetric trimers (isocyanurates) and asymmetric trimers (iminooxadiazinediones).
  • trimer mixture is defined as the sum of symmetric trimers (isocyanurates) and asymmetric trimers (iminooxadiazinediones).
  • the products which can be prepared in that manner may occasionally also exhibit a high level of turbidity (greater than 1.5 TE(F) when measured using a device from Hach).
  • the actual catalytically active species which yields different products according to the type of reaction (normal versus abnormal in the sense of the preceding description), forms only during the reaction from the ammonium polyfluoride that is added, as a result of the effect of the isocyanate to be oligomerized or the secondary products present in these isocyanates.
  • An object of the present invention is to provide a reproducible process which is not subject to the above-mentioned incalculabilities such that
  • This object may be achieved by the process according to the invention by catalyzing isocyanate trimerization with quaternary phosphonium polyfluorides.
  • the present invention relates to a process for the preparation of trimerized polyisocyanates that contain at least 30 mole % of iminooxadiazinedione groups (asymmetric trimers) in the trimer mixture, by catalytically trimerizing a starting isocyanate selected from organic di- or polyisocyanates having a number average molecular weight of 140 to 600 and containing aliphatically, cycloaliphatically and/or araliphatically bound isocyanate groups in the presence of a quaternary phosphonium polyfluoride trimerization catalyst corresponding to the formula
  • R represents identical or different, optionally branched aliphatic, aromatic and/or araliphatic C 1 -C 20 groups, or two or more R groups may also form, with one another and with the phosphorus atom, saturated or unsaturated rings and
  • n has a value of 0.1 to 20.
  • FIG. 1 represents a graph of heat production vs. time for a prior art trimerization reaction.
  • FIG. 2 represents a graph of heat production vs. time for an embodiment of the trimerization reaction according to the invention.
  • trimer mixture includes both isocyanurate and iminooxadiazinedione groups.
  • the process in which there are used as the isocyanate component to be trimerized aliphatic diisocyanates having a molecular weight of 140 to 300 in the form of pure compounds or mixtures of these compounds.
  • the products of the process preferably contain at least 35%, more preferably at least 40 mole % of iminooxadiazinedione groups (asymmetric trimers) in the trimer mixture.
  • the quaternary phosphonium polyfluorides trimerization catalysts are used in admixture with alcohols having a molecular weight of 32 to 250 g/mol.
  • the trimerization catalysts may either be used as pure compounds or as mixtures of compounds of the formula R 4 P + F - n(HF), wherein R represents identical or different, optionally branched, aliphatic, aromatic and/or araliphatic C 1 -C 20 groups.
  • R groups may optionally be substituted.
  • suitable catalysts include products which are commercially available, optionally in the form of their salts with counterions other than polyfluoride, which can readily be converted into the polyfluoride form, such as chlorides, bromides, iodides and (hydrogen) sulfates. See, for example, Synthesis 1988, 12, 953-955 and Example 1.
  • Examples include tetrakis(hydroxymethyl)phosphonium chloride and sulfate; and tetraethyl-, tetrabutyl-, tetraoctyl-, tetrakis(hexadecyl)-, tributyl(tetradecyl)-, tributyl(hexadecyl)- and trioctyl(octadecyl)-phosphonium chloride, bromide or iodide.
  • catalyst solvents are usually required for their use in the isocyanate trimerization according to the invention.
  • these solvents include straight-chain and branched, primary, secondary and tertiary alcohols having 1 to 20 carbon atoms, preferably 1 to 8 carbon atoms, such as methanol, ethanol, n- and iso-propanol, 1- and 2- butanol, isobutanol and 2-ethylhexanol.
  • Triphenyl(alkyl) derivatives may also be used, although they are less preferred due to their poorer solubility in the previously mentioned solvents, especially alcohols, when compared to the purely aliphatically substituted catalysts (Examples 1c and 3-15).
  • EP-A 0,315,692 which describes concept of phase transfer catalysis, potassium fluoride-catalyzed processes for the preparation of compounds having isocyanurate groups are described. The simultaneous presence of phosphonium compounds to "increase the efficiency of the reaction" is also proposed. Polyfluorides are not mentioned. Also, phosphonium salts are not used in the examples.
  • the specification primarily relates to the trimerization of aromatic isocyanates (TDI, MDI). The trimerization of isocyanates containing aliphatically bound NCO groups to form isocyanurate groups is only demonstrated by the reaction of n-butyl isocyanate with potassium fluoride in two examples. In Examplel of EP-A 0,315,692 potassium fluoride was used as the sole catalyst; in Example 5 potassium fluoride was used in the presence of a quaternary ammonium salt (benzyltrimethylammonium chloride.
  • EP-A 235,388 describes a process for the preparation of mixed isocyanate-polycarboxylic acid/polycarboxylic acid anhydride secondary products using alkali metal fluorides as catalysts with the simultaneous presence of quaternary onium salts.
  • alkali metal fluorides as catalysts with the simultaneous presence of quaternary onium salts.
  • activated complex the formation of the actual catalytically active species ("activated complex") from the original catalyst molecule and isocyanate group(s) in the presence of excess starting isocyanate can be fulfilled in a considerably better and, especially, more reproducible manner by the phosphonium catalysis according to the invention instead of the corresponding ammonium compounds.
  • n in formula (I) is not critical; however, for practical considerations and also because of the unpleasant physiological properties of hydrogen fluoride, it is not used in large molar excesses, based on fluoride (F - ) present, even though these excesses are suitable for preparing polyisocyanates having a high iminooxadiazinedione content. Even a catalyst system having a 20 times molar excess of hydrogen fluoride, based on fluoride (F - ) present, yields products which are perfect in terms of quality and have a high iminooxadiazinedione content (over 50 mole % in the trimer mixture, Examples 3-11 to 3-13).
  • the process according to the invention is carried out at a temperature of 20° C. (room temperature) to 200° C., preferably 30° C. to 120° C. and more preferably from 40° C. to 100° C., with proportional reaction of the isocyanate groups of the starting isocyanate.
  • the degree of reaction R NCO which is calculated as the quotient of the difference between the NCO content of the starting isocyanate before trimerization and the NCO content of the reaction mixture after termination of the reaction divided by the NCO content of the starting isocyanate before trimerization, is 5% to 60%, preferably 10% to 40%.
  • Any unreacted monomer may, after deactivation of the catalyst system, be separated off by any known method, for example, by (thin-layer) distillation or extraction, and then recycled.
  • any of the known prior art methods for terminating the trimerization reaction with isocyanurate formation may be used. Examples include the addition of less than, equal to or greater than stoichiometric amounts of strong acids or acid derivatives with respect to the molar amount of fluoride (MW 19) used (e.g., benzoyl chloride, phosphorous and phosphoric acid and acid esters thereof, but not HF), adsorptive binding of the catalyst and subsequent removal by filtration and thermal deactivation.
  • fluoride e.g., benzoyl chloride, phosphorous and phosphoric acid and acid esters thereof, but not HF
  • the removal of excess starting (di)isocyanate, provided that it is a low molecular weight "monomeric" (di)isocyanate, is preferably carried out when the products of the process according to the invention are intended for use in the polyurethane lacquer and coating compositions.
  • the excellent color index and color stability of the products, as well as their high resistance to cleavage to reform the monomeric starting (di)isocyanate, are advantageous.
  • catalyst concentrations (based on the weight of the starting isocyanate and the fluoride ion, MW 19) of 1 ppm to 1%, preferably 1 ppm to 0.1% and more preferably 1 ppm to 0.05%, are sufficient.
  • the oligomerization is carried out in a tube reactor.
  • the very low tendency of phosphonium polyfluoride catalysts to form gel particles in the product, even when used in highly concentrated solution or in pure form, is an advantage in this process.
  • Suitable organic compounds include those that are inert towards NCO groups, such as toluene, xylene(s), higher aromatic compounds, esters, ethers, ketones, C 12 -C 20 -alkylsulfonic acid esters and mixtures thereof.
  • Suitable starting isocyanates for carrying out the process according to the invention include di- or polyisocyanates having a number average molecular weight of 140 to 600 and containing aliphatically, cyclo-aliphatically and/or araliphatically bound isocyanate groups.
  • the starting isocyanates may be used in pure form or in the form of mixtures.
  • HDI hexamethylene diisocyanate
  • MPDI 2-methylpentane-1,5-diisocyanate
  • IMCI 1,3-bis(isocyanatomethyl)-cyclohexane (1,3-H 6 -XDI)
  • IMCI 3(4)-isocyanatomethyl-1-methyl-cyclohexyl isocyanate
  • IPDI isophorone diisocyanate
  • NBDI bis(isocyanatomethyl)-norbornane
  • TIN 4-isocyanatomethyl-1,8-octane diisocyanate
  • TIN 1,3-bis(isocyanatomethyl)-benzene
  • 2-isocyanatopropyl-2)benzene 1,3-bis(2-isocyanatopropyl-2)benzene and bis(4(2)-isocyanatocyclohexyl)methane
  • H 12 MDI Desmodur W, available from Bayer AG
  • the process used for preparing the starting isocyanates i.e., with or without the use of phosgene, is not important.
  • Preferred starting isocyanates are HDI, MPDI, 1,3-H 6 XDI, NBDI and mixtures of HDI and IPDI.
  • mixtures of starting isocyanates in the process according to the invention, for example, in order to satisfy the property requirements for the product.
  • polyisocyanate mixtures based on optionally branched, linear-aliphatic diisocyanates such as HDI and cycloaliphatic diisocyanates such as IPDI or H 12 MDI are used.
  • These mixtures are generally prepared by the mixing polyisocyanates that have been separately prepared from the two types of starting diisocyanates.
  • it may be advantageous to prepare them by simultaneous mixed trimerization from the corresponding mixture of the monomeric components EP-A 0,047,452).
  • polyisocyanates based on the known cycloaliphatic diisocyanates are solid. They occasionally have such a high melt viscosity that separation of the monomers by (thin-layer) distillation presents considerable difficulties. For that reason, solvents or flow additives must be used during their processing and sometimes occasionally, also for thin-layer distillation. If too great a loss in the degree of reaction (resin yield) and NCO functionality in the preparation of these polyisocyanates is not acceptable, the resulting isocyanurate polyisocyanates based on cycloaliphatic diisocyanates have solution concentrations of about 70% resin solids and readily processable dynamic viscosities of 1 to 10 Pa ⁇ s (23° C.).
  • the products and product mixtures obtained by the process according to the invention are suitable starting materials for a variety of uses, including the manufacture of optionally foamed plastics as well as lacquers, coating compositions, adhesives and additives.
  • the products of the present invention may optionally be modified by reacting the isocyanate groups to incorporate urethane, urea, biuret and/or allophanate groups or by reacting some or all of the NCO groups with reversible blocking agents.
  • Suitable blocking agents include phenols, lactams such as ⁇ -caprolactam, oximes, di- and triazoles, amines such as diisopropylamine and CH-acid compounds such as malonic acid dialkyl esters and acetoacetic ester.
  • the products prepared according to the invention are especially suitable for the manufacture of optionally water-dispersible one- and two-component polyurethane coating compositions because their solution and melt viscosities are reduced when compared to isocyanurate-polyisocyanates, while their properties profile is equally high or is improved. Therefore, the HDI-based products of the invention are more stable towards the occurrence of flocculation or turbidity, even when highly diluted in lacquer solvents, when compared to the known corresponding products containing mainly isocyanurate groups.
  • Dynamic viscosities were determined at 23° C. using a VT 550 viscosimeter from Haake. By means of measurements at different shear rates it has been ensured that the flow properties of the described polyisocyanate mixtures according to the invention, as well as those of the comparison products, correspond to those of ideal Newtonian fluids. It was therefore unnecessary to indicate the shear rate.
  • Residual monomer contents were determined by gas chromatography.
  • the turbidity of the trimer resins was determined using a device from Hach. To that end, scattered light measurements were carried out at 90° to the direction of a light beam having a wavelength of from 400 to 800 nm guided through the resin sample, and were given in units based on formazine standard solutions, TE(F).
  • the mixture was liquid at room temperature and solidified to a white crystal-line composition only when stored in a deep freeze (-12° C.).
  • the composition became virtually completely liquid again even when subsequently stored in a refrigerator (-2° C.) (turbid solution containing solids particles).
  • Subsequent storage at room temperature (20-25° C.) again yielded a homogeneous, clear, colorless solution having the above-mentioned analytical data.
  • stock solution 2 The highly concentrated solution so obtained (hereinafter stock solution 2) was used for HDI trimerization as such (Example 3-0) as well as in admixture with various alcohols, with further HF or with further phosphonium fluoride (see Example 3, Table 1).
  • the mixture was then filtered and the filtration residue was washed with 2 ⁇ 50 g of commercial methanol; a further 50 g (0.86 moles) of powdered potassium fluoride was added to the combined filtrates, and stirring was carried out for 24 hours at 20-25° C. (room temperature).
  • the mixture was largely freed of excess methanol and isopropanol in a rotary evaporator at a maximum temperature of 30° C. and a pressure of approximately 1 mbar, and filtration was carried out again.
  • the resulting solution had the following properties:
  • HDI trimerization using a quaternary ammonium hydrogen difluoride catalyst 1 (DE-A 19,611,849 or U.S. Pat. No. 5,914,383).
  • the reaction was terminated by the addition of 150 mg of dibutyl phosphate and the reaction mixture was analyzed.
  • the proportion of iminooxadiazinedione in the trimer mixture was 9.5 mole %.
  • the trimer resin obtained after thin-layer distillation using a laboratory thin-layer evaporator, of the short-path evaporator type, at 140°/0.2 mbar had the same low iminooxadiazinedione content and exhibited relatively high turbidity (10.2 TE(F)).
  • Example 3-1 in Table 1; see also FIG. 2).
  • R NCO was approximately 20%; the reaction was terminated by the addition of a molar amount of dibutyl phosphate, which corresponded to the F - consumption.
  • the F - requirement of the reaction at 1st/2nd/3rd additions of catalyst is shown in FIG. 2, i.e., 40/20/11 ppm of F - , based on the weight of HDI and the fluoride ion F - (MW 19, not total fluorine).
  • the molar ratio of iminooxadiazinediones to isocyanurates was approximately 45:55.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Saccharide Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Compounds Of Unknown Constitution (AREA)
  • Separation Of Suspended Particles By Flocculating Agents (AREA)
US09/318,537 1998-06-02 1999-05-25 Process for preparing polyisocyanates containing iminooxadiazinedione groups Expired - Lifetime US6090939A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE1998124485 DE19824485A1 (de) 1998-06-02 1998-06-02 Verfahren zur Herstellung Imidooxadiazindiongruppen enthaltender Polyisocyanate, die so hergestellte Verfahrensprodukte und ihre Verwendung
DE1998124490 DE19824490A1 (de) 1998-06-02 1998-06-02 Verfahren zur Herstellung Imidooxadiazindiongruppen enthaltender Polyisocyanate, die so hergestellte Verfahrensprodukte und deren Verwendung
DE19824485 1998-06-02
DE19824490 1998-06-02

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Cited By (44)

* Cited by examiner, † Cited by third party
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US6515097B2 (en) 2000-12-14 2003-02-04 Bayer Aktiengesellschaft Blocked polyisocyanates based on HDI
US20030109665A1 (en) * 2001-12-07 2003-06-12 Degussa Ag Catalysts for preparing polyisocyanates containing isocyanurate groups, and their use
FR2833864A1 (fr) * 2001-12-21 2003-06-27 Rhodia Chimie Sa Catalyseur de condensation pour isocyanate, composition en contenant, procede d'utilisation, et compositions obtenues
US20030135007A1 (en) * 2001-12-05 2003-07-17 Degussa Ag Catalysts for preparing polyisocyanates containing isocyanurate groups, and their use
WO2004078820A1 (en) * 2003-02-28 2004-09-16 Dow Global Technologies Inc. Preparation of isocyanurate group containing polyisocyanate mixtures
US20040242741A1 (en) * 2003-05-20 2004-12-02 Christian Wamprecht High-solids binder combinations for scratch-resistant topcoats
US20050027095A1 (en) * 2003-07-30 2005-02-03 Christian Wamprecht New binder combinations for highly resistant plastic paints
US6894138B1 (en) 2003-11-26 2005-05-17 Bayer Materialscience Llc Blocked polyisocyanate
US20050113548A1 (en) * 2003-11-26 2005-05-26 Roesler Richard R. Solid powder coating crosslinker
US7205356B2 (en) 2003-02-26 2007-04-17 Bayer Materialscience Ag 2-K PU systems
US20070149750A1 (en) * 2003-11-26 2007-06-28 Bayer Materialscience Llc Solid powder coating crosslinker
US20070269661A1 (en) * 2006-05-16 2007-11-22 Graham William F Ultraproductive coating composition using a chemically mixed isocyanate system
US20070282070A1 (en) * 2006-05-16 2007-12-06 Adams Jerome T Highly productive coating composition for automotive refinishing
US7595396B2 (en) 2004-10-07 2009-09-29 Bayer Materialscience Ag Process for preparing polyisocyanates containing iminooxadiazinedione groups
US20100076152A1 (en) * 2004-11-25 2010-03-25 Bayer Materialscience Ag New polyisocyanate mixtures, a process for their preparation and their use in coating compositions
US20100099816A1 (en) * 2008-10-22 2010-04-22 Bayer Materialscience Ag Moisture-curing polyisocyanate mixtures
US20100203241A1 (en) * 2009-02-12 2010-08-12 Bayer Materialscience Ag Prepolymer-Based Polyurethane Formulations For The Production Of Holographic Films
US8802771B2 (en) 2010-11-22 2014-08-12 Dow Global Technologies Llc Two component polyurethane coating compositions comprising isocyanurate compositions from bis(isocyanatomethyl) cyclohexane and from aliphatic diisocyanates
US20140275525A1 (en) * 2011-11-29 2014-09-18 Bayer Intellectual Property Gmbh Method for producing polyisocyanates and use thereof
US9458318B2 (en) 2010-07-20 2016-10-04 Covestro Deutschland Ag Polyisocyanate mixtures
US9458097B2 (en) 2010-08-03 2016-10-04 Covestro Deutschland Ag Process for the preparation of polyisocyanates and use thereof
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BR9902634A (pt) 2000-03-21
CN1140518C (zh) 2004-03-03
KR100580425B1 (ko) 2006-05-16
CA2272761A1 (en) 1999-12-02
EP0962454A1 (de) 1999-12-08
EP0962455B1 (de) 2002-11-06
ATE225777T1 (de) 2002-10-15
CA2272755A1 (en) 1999-12-02
JP2000086640A (ja) 2000-03-28
JP4538112B2 (ja) 2010-09-08
ES2185265T3 (es) 2003-04-16
BR9902634B1 (pt) 2009-05-05
ES2187097T3 (es) 2003-05-16
PT962454E (pt) 2002-12-31
KR20000005770A (ko) 2000-01-25
JP2000034284A (ja) 2000-02-02
JP4519217B2 (ja) 2010-08-04
US6107484A (en) 2000-08-22
BR9901691A (pt) 2000-03-21
CN1243124A (zh) 2000-02-02

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